3-Methoxyaniline → HCID 43121631, compound

Participants

Reaction Steps

(Method 2A) A solution of 1-azabicyclo[2.2.2]octan-3-one (8.1 g, 50 mmol), m-anisidine (6.2 g, 50.0 mmol) and 4Å molecular sieves in 50 mL of EtOH was stirred at room temperature overnight. NaBH4 pellets were added until the reaction was judged complete by TLC, at which point most of the EtOH was evaporated in vacuo and the residue was partitioned between 3N NaOH and EtOAc. The aqueous layer was extracted with a second portion of EtOAc. The organic layers were combined and washed with water and then brine and then dried over NaSO4. The solution was filtered and the solvent was evaporated in vacuo. The residue was dissolved in 2-PrOH and treated with 1.5 g of fumaric acid. The product was collected and recrystallized from 2-PrOH to give N-(3-methoxyphenyl)-1-azabicyclo[2.2.2]octan-3-amine (5.2 g, 30%) as an intermediate, an off-white solid. MH+=233.

Provenance & Evidence